Tetrabutylammonium Fluoride → Tert-butyl 3-((7-chloropyrido[4,3-b]pyrazin-5-ylamino)methyl)-5-hydroxypiperidine-1-carboxylate

HRID 57538Notes

Reaction equation

HRID 57538 reaction equation
[Si]([O:8][CH:9]1[CH2:14][CH:13]([CH2:15][NH:16][C:17]2[C:26]3[C:21](=[N:22][CH:23]=[CH:24][N:25]=3)[CH:20]=[C:19]([Cl:27])[N:18]=2)[CH2:12][N:11]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:10]1)(C(C)(C)C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1.C(OCC)(=O)C>[Cl:27][C:19]1[N:18]=[C:17]([NH:16][CH2:15][CH:13]2[CH2:14][CH:9]([OH:8])[CH2:10][N:11]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:12]2)[C:26]2[C:21](=[N:22][CH:23]=[CH:24][N:25]=2)[CH:20]=1

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 86717367Tert-butyl 3-(tert-butyldimethylsilyloxy)-5-((7-chloropyrido[4,3-b]pyrazin-5-ylamino)methyl)piperidine-1-carboxylate

Product 1

HCID 86717368Tert-butyl 3-((7-chloropyrido[4,3-b]pyrazin-5-ylamino)methyl)-5-hydroxypiperidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of tert-butyl 3-(tert-butyldimethylsilyloxy)-5-(7-chloropyrido[4,3-b]pyrazin-5-ylamino)methyl)piperidine-1-carboxylate from step E in THF (16 mL) was treated with TBAF (5.17 g, 16.4 mmol) at room temperature for 2 hours, then diluted with ethyl acetate, washed with brine, dried over Na2SO4, filtered, and concentrated. The residue was purified by chromatography to give the title compound. MS (m/z): 394 (M+H)+.

Workup

  1. washwashed with brine
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by chromatography

Sources & evidence

ORD record
ord-7831a9416fc54747941937af883cbc77
Source dataset
uspto-grants-2016_09
Patent number
US09434726B2

Reaction notes

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